SAN DIEGO — The sound of rock ’n’ roll is the sound of romance and rebellion, and there are no greater romantic rebels than Romeo and Juliet, Shakespeare’s heedless young lovers, who defy the authority of their warring tribes, marry in secret, and willingly embrace the dark fate that unhappy circumstance has ordained for them. “The Last Goodbye,” a new musical adaptation of the play at the Old Globe Theater here, audaciously attempts to find the spiritual kinship between Shakespeare’s tragedy and the keening angst in the music of Jeff Buckley, the singer-songwriter who died in 1997 at the age of 30, as his promising career was gaining momentum.

Conceived and adapted by Michael Kimmel, the production is directed by the busy Alex Timbers. (Next up: the musical version of “Rocky.”) Mr. Timbers created a similar mash-up of Shakespeare and pop over the summer in Central Park, with his frolicsome collegiate update of “Love’s Labour’s Lost,” featuring original songs by Michael Friedman. There’s a signal difference between the two projects, of course: One play is a comedy, one a tragedy. Comedy, though famously hard to pull off, doesn’t require the depth of feeling that tragedy does, obviously. And while I thoroughly enjoyed Mr. Timbers and Mr. Friedman’s freewheeling reimagining of “Love’s Labour’s Lost,” I felt emotionally shortchanged by “The Last Goodbye,” despite the natural affinities between Buckley’s music, which sings with a throb in the throat of love’s tribulations, and the doomed passion of Romeo and Juliet.

The production has a stylish contemporary look. In their black rubberized denim and sleekly cut leather and wool jackets, the young Capulets and Montagues might have come straight from a photo shoot for a John Varvatos ad campaign. (The costumes are by Jennifer Moeller.) Christopher Barreca’s moody sets are dominated by a series of stone arches suggestive of ruined aqueducts, trimmed in neon that glows red, blue and purple.

“The Last Goodbye” whips through the story. Even with about 15 of the songs Buckley wrote (or recorded) interpolated into the original text, the show does indeed constitute about “two hours’ traffic” of stage time, including an intermission. Virtually all the machinery of the plot is kept, so the headlong pace necessarily means that Shakespeare’s text has been heavily cut. Secondary characters become almost incidental: the Nurse’s comic loquacity is gone, and Mercutio, played by Hale Appleman as a louche, androgynous troublemaker (at one point he romps around in a fluffy fake fur) doesn’t get to rhapsodize about Queen Mab.

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Their flirtatious first exchange is likewise trimmed, and ends abruptly with a long, scorching kiss, as in the current Broadway “Romeo and Juliet.” In the balcony scene, the besotted lyricism of Juliet becomes a greatest-hits medley: we go from “Wherefore art thou Romeo?” to “Parting is such sweet sorrow,” while tasting too little of the sweet meat in between.

This is, of course, because Buckley’s “All Flowers in Time” becomes the primary motif establishing the sudden blooming of their love. It’s a pretty song, and in both lyric and melody suits the wonder-struck mood. (The chorus runs: “All flowers in time bend toward the sun/I know you say there’s no one for you/But here is one, here is one.”) Here and in other instances, Mr. Kimmel and Mr. Timbers have woven together Buckley’s lyrics and Shakespeare’s verse with ingenuity.

But does what is gained make up for what is lost? The emotional resonance and depth of character established by Shakespeare’s verse must be supplied by Buckley’s music, and that’s a mighty heavy burden to put on any composer. (Even Leonard Bernstein’s symphonic music for “West Side Story” didn’t have to brush up against Shakespeare.) In the less important scenes, you don’t so much mind. The riotous “Witches’ Rave” effectively establishes the tense atmosphere of incipient conflict at the Capulets’ ball, as well as the anything-goes feeling that might lead to a sudden infatuation.

But when it comes to the big moments, Buckley’s lilting melodies and his forthright lyrics don’t have the theatrical heft to capture the intensity of feeling that’s required, despite the elegant, guitar-led orchestrations by the music director Kris Kukul. The music of Green Day, in “American Idiot,” and of Duncan Sheik, in “Spring Awakening,” held the stage more naturally. Buckley’s songs too often feel like earnest but glib place holders for the greater emotional range and expressiveness of the verse.